Family-friendly holiday rentals in Fleming Island

5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

Stellar location...easily park and walk to historic sites! Spacious and modern inside but a classic Southern home on the outside. Lots of room to grill out or lounge around the heated saline pool. Beautiful views of the famed Mission from the upper/lower porches. And you'll appreciate how well stocked this home is too...if we don't provide it you probably don't need it! If you need another rental we have a 4 bedroom w/pool right next door. It's called Walk to Everything plus pool and Cottage.

4.98 out of 5 average rating, 175 reviews

Serenity Now - On The Beach

Welcome to Serenity Now! This immaculate beachfront home was completely renovated with beautiful, new furniture and comfortable beds. Sleeps 10 easily in 5 bedrooms, 2.5 baths & hot, outdoor shower. Fully equipped kitchen & BBQ for easy family meals. Enjoy covered, wrap around decks & ocean views from nearly every room! Keyless entry & self check-in. *Service/emotional support animals not allowed b/c our family is severely allergic. 5/27-8/17 weekly rentals; but inquire for shorter stay.

Superhost

4.77 out of 5 average rating, 126 reviews

Oceanside/pool view-Surf Crest Village-Pets welcom

This Beach Cottage has all the charms and amenities that you want for your vacation. HDTV with DVD's for those rainy afternoons, sit in the cabana on the beach, read a book, or go for a swim in the seasonally heated pool . We even have a high chair for small family members. You are 200 yards from the beach, and walking distance to putt putt, and 20 different restaurants. 2 bedrooms with bath/kitchen/living area on top floor, and a private living area w/2 bedrooms & bath downstairs as well.

Townhouse in St. Augustine

4.91 out of 5 average rating, 128 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

Superhost

4.85 out of 5 average rating, 233 reviews

1st street, Cedar Beach House Retreat

Completely Renovated Beach house, 2 blocks from the Ocean on St. Augustine's most magical beach. Backyard has seasonal Fruit trees, seating area, shower, private Hot Tub, & BBQ. Front has a covered sitting area & 240 volt EVs. charger. Blinds on widows in all bedrooms. Located a couple of blocks to great spots to eat & drink or a short stroll to the Beach. 14 minute drive/28 minute bike ride to the historic downtown landmarks. Bike to Amphitheater. WIFI enabled, 200 mbbs internet speed

4.93 out of 5 average rating, 122 reviews

Home in Beaches

Luxury Beach Getaway w/ Heated Pool & Game Room

Recently built gorgeous 5-bedroom beach house with heated pool and game room with pool table, foosball, dart, shuffleboard, and ping pong. Living rooms on each level. Great for families. Gourmet chef's kitchen with 5 burner gas stove. Cable TV with all movie channels provided. Includes a putting green, bocci court, outdoor dining under the covered patio and a smart TV. BIKES INCLUDED PET FRIENDLY: We warmly welcome four-legged CANINE friends. No cats, please. (They don't like the beach!)

Townhouse in St. Augustine

4.96 out of 5 average rating, 107 reviews

***Direct Beachfront Oceanfront~Incredible Views!

Located on Vilano Beach, St. Augustine, FL, this three-story townhome is waiting to make memories for you and your family. Located directly on the beach-designed to envelope the soul in tranquility, this three-story townhome includes three lovely bedrooms. The main floor boasts a gourmet kitchen, half bath, laundry room, family room, dining area, and ocean viewing area. A laundry room houses a full size washer and dryer. Ultra high speed Internet is provided and reaches to the beach!

Home in Southeast Jacksonville

4.95 out of 5 average rating, 184 reviews

The confetti house - 1 mile from the Mayo clinic!

Cozy home located in a quite and safe neighborhood. 3 1/2 miles from the beach, 1 mile to the Mayo clinic, 5 miles to the Town Center, 1 1/2 miles to a marina and 1 mile to a state preserve with access to the intracoastal water ways. Walking distance to a park with tennis courts and playground for children. Adventure Landing waterpark is 2.5 miles away. 1 mile walking distance to stores and restaurants. Enjoy a cup of coffee in the screened in lanai listening to the Koi pond waterfall!

4.85 out of 5 average rating, 275 reviews

Sunny, family friendly Sol Mate Beach Cottage

Our renovated beach cottage is one block to the beach, walking distance to restaurants and ice cream, nightlife, public transport, family-friendly activities. Across the street is the pier, volleyball courts, splash pad and weekly Wednesday farmers market. A short drive to the oldest city in the US and a grocery store! You’ll love our adorable beach cottage because of the location, the neighborhood and the beach is gorgeous. Our place is good for couples, solo adventurers, and families.

Apartment in St. Augustine

4.91 out of 5 average rating, 170 reviews

Unwind, relax and enjoy! King bed - beach items

St. Augustine Beach is the hidden gem of northeast Florida! Family and pet-friendly condo within walking distance to the pristine white sand beaches, fishing pier, local shops and restaurants. Sandy Feet Retreat is a 2 bedroom / 2 bath air-conditioned unit that sleeps up to four guests. Walk into the inviting living room where you’ll find tasteful beach decor, a classic surf board on the wall, a unique mermaid light, as well as comfortable sofas and a 50-inch LCD Smart TV and WiFi.

Townhouse in St. Augustine

4.9 out of 5 average rating, 262 reviews

St. Augustine Beach - A Townhouse Oasis!

Guests will discover a warm, inviting townhouse that aims to meet the needs of your vacation getaway. See for yourself why many of the same families rent this townhouse year after year for its quality and value. As hosts, we maintain and provide an up to date, comfortable, and convenient location to all the sites in the greater St. Augustine area; including a convenient 5-6 minute walk to the beach. ALSO, IF YOU LIKE YOUR PRIVACY you will enjoy our screened-in roof-covered lanai.